Cross Dressing
Not so much a 'stupid' dare, but a dare nonetheless... the stupidity lies in loss of respect over the following months. My college has a yearly haloween party that involves cross dressing - all the men dress as women, and the women look worried as previously 'macho' guys worry about whether a dress makes them look fat.

Naturally, this leads to men being dared to wear the most obscene costumes possible. In my first year a group of ice hockey players were dared to dress as the East German Womens Swimming Team. They turned up in bikinis, with abundant mounds of excess fake hair pouring from every possible seam. There was also a group of playboy bunnies... some of whom were almost hairy enough to pass for a real bunny.

Last year was more restrained, but this year (and its starting in about 3 hours) I know of one guy who has been dared to buy one of those Anne Summers schoolgirl outfits and to wear it to the party. We'll see if he has actually gone through with it. Apparently it has an incredibly short skirt and a pair of knickers with 'spank me' written across the seat. Think he's going to get away without being spanked in a room full of drunken men-women? The poor bastard could end up being molested by cross dressing drunkards... if that isn't stupid I don't know what is.

Luckily I haven't been dared at all, and so am restrained in a delightful pink and black off the shoulder number, complete with a 'miss naughty' sash, and a far too excited female friend who is coming over in an hour or so to paint me 'like a whore'. I'm 6 foot 6 and over 20 stone... its going to be beautiful. At least this year I don't have a beard.
(Zapiola zip-zap-zop, Sat 3 Nov 2007, 17:50, 1 reply)

Well?
So post a follow-up!
( The Resident Loon Not a demographic. Do not measure., Sun 4 Nov 2007, 0:08, closed)